


Sissy Boy to Pretty Girl

by ThePrincessOfPirates



Category: Space Quest (Video Games), Space Quest 6: Roger Wilco in the Spinal Frontier
Genre: Crossdressing, Crossdressing Kink, Drag Queens, Drinking, F/M
Language: English
Status: Completed
Published: 2016-12-27
Updated: 2016-12-27
Packaged: 2018-09-12 13:21:23
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,170
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9073726
Author URL: https://archiveofourown.org/users/ThePrincessOfPirates/pseuds/ThePrincessOfPirates
Summary: Why not haze the new recruits? Let's start with Janitor Second Class; Roger Wilco.





	

“Here comes REGINA!!!” The navigator slams his fists on the table, only the strength of the whole ordeal keeping the drinks down. This had started out as a joke, a suggestion of some weird hazing ritual to initiate the lower ranks into the crew. Someone mentioned something about forcing Roger to do it since he was not only fairly new but also a janitor.

“Your enough of a sissy to do it, right, Wilco. Rodger!” The humanoid engineer shook his shoulder. The young man had shiny golden eyes and though his skin was peach, it shined blue under the sweat and light.

“What? Sorry, I wasn't listening.” Rodger smiled nervously.

“Dress up in drag and do a walk down the bar. Strut your stuff for the whole crew.” His ears, which were pointy and long, twitched.

“Well I don't know...” Roger could feel the blush rising on his face.

“Come on,” the other man near him was taller and more muscular but had gills and claws. “What sort of face do you really have to save?”

“He has a point, Roger.” Sydney, not being capable of drinking, was awkwardly sitting at a bar stool. “I mean, you don't have to do anything you don't want to, but it could be quite an enjoyable group activity.”

“Save me this one scrap of my dignity.” Roger crossed his arms, determined to stand his ground.

“Could 50 buckazoids persuade you?” The girl was from the medical department and had flowing, tight curls and big green eyes.

“You got me there... But I don't even own any girls dresses only...” He cut himself off.

“Only what?” She leaned in further towards him. “Only those panties that you think don't leave an outline under your pants? Because for the record, they're very noticeable when you bend down.”

“In my defense, that whole ordeal's more about the feel than cross-dressing. They're just... Softer.” Roger was tense and trying to remove himself from this torment.

“Come on, I can get you prettied up in 30 minutes and I think I've got something that'll fit you.” She grabbed onto his sleeve and pulled him towards the transporter.

He fell with a thud to the floor of her room. It was much cleaner than his, ironically.

“Hey what's your name anyway?” He stood up and looked around. Pretty standard digs for StarCon crew except for the few extras here and there and lots of clothes as decoration.

“I'm Kaldiva, you can call me Diva.” The door to her closet slid open and it was filled to the brim with uniforms and dresses, an even 50/50 of the two.

“And why are you so eager to get me into a dress, Diva?” Roger put his hands on his hips and sauntered closer to her.

“Because there's nothing I love more than helping someone have a good time. I knew I could help you have an evening that quite a few people will find satisfying. I'm a facilitator, you might say.” She skimmed through the dresses, looking each one over before moving onto the next.

“So you like to help people make bad decisions. Great, I make plenty of those on my own.” Roger huffed, sitting down in a lounge chair in the room.

“No, I like helping people make decisions. I help the wilder path seems more approachable. Do you have a color preference?” She appeared to be grouping a few dresses together.

“I'll take whatever you have that'll fit me.” Roger shrugged, enjoying how everything in the room had it's place yet still looked... Used. The sheets were rumpled, the desk had notebooks and pencils strewn atop it.

“Alright, I think I found something. For future reference, you are probably a size 8-10 in women's dresses.” She pulled out from the closet a long sleeved, off the shoulder, silver holographic, body-con dress.

“Shiny!” Roger chuckled.

“Put it on, I'll grab you some stockings. Fishnets are really good for disguising the fact that you haven't shaved.” She started heading for another set of cabinets.

“I have shaved recently.” The moment he said it she stopped in her tracks.

“How recently?” She turned to face him.

“Earlier today.” It was a little embarrassing to admit it, but he just preferred having his legs smooth and it wasn't like he had a real job to get to after he showered in the morning. Plus, he could use it as an excuse for being late in the mornings since his supervisor didn't understand human customs well enough to know that it was out of the ordinary.

“Amazing!” Diva looked overjoyed. “Do you know how to tuck? That dress kinda requires it unless you really want to leave nothing to the imagination.”

“I guess I know how it works theoretically, but I'm absolutely terrified of it.” He shuddered a little at the thought.

“You really are going to do this? Wasn't the last game enough of an embarrassment for you? Sometimes I think you get off to being a laughing stock!” That voice in the back of his head, the one that sometimes other people could hear, always chimed in at times like these.

“Oh can it you cigarette salesmen!” Roger mumbled under his breath.

“What was that?” She turned towards him, stalling from rooting through the drawers.

“Nothing just... Talking to myself.” He smiled weakly.

“Well, I guess if it makes you feel better.” Diva brushed off the incident like it was nothing. “Alright slip into these-” she tossed a pair of spandex panties at him. “You don't have to full on tuck, those will kinda hold you in place if you know what I mean. I'll get your some shoes. What size are you?”

“Men's 9 and a half. Why do you have so many clothes if they aren't all in your size? You've got a library of dresses here in everything from small to 2XL.” There were gowns draped on the walls and shoes lined around the perimeter of the room.

“I'm a sucker for a good game of dress-up and I'm not always the one playing dolly.” She looked at him as if it was no big deal and bent down for a pair of platforms. “Start getting dressed, we don't have long if we want to get back there soon.”

“I mean no offense but I'd rather not change with you still in the room.” Roger fiddled with the hem of his shirt as he stood up.

“I'll step into the bathroom to get makeup then, no biggie.” The shoes clunked as they land in the chair behind him.

The clothes are new and not his and it's weird to put on clothes that aren't yours. The dress is a snug fit but once he's got it on, it soft and comfortable. He looks himself up and down in the mirror, a large feather boa hanging on one side. He looks... Nice? It's tight around what little hip he has and even though he has no chest to speak of, the dress pulls taught there and it looks right.

“Like the fit?” The bathroom door slid open and Diva stepped out holding a surprisingly small amount of makeup.

“It still makes my body look masculine.” His eyes dart over to her nervously.

“That's the point. Personally I think we're going to turn the most heads if your stunningly gorgeous but still, undeniably male. Make a few boys and girls question their sexuality” She shook a small opaque bottle of something idly. “Now I've gotta ask, since I'm about to cover your face in glitter, you know why I agreed to help you but we're in a little too deep for this to be just 50 buckazoids to you.”

“Sweetheart, you don't even know the things I've done for 50 buckazoids. I've set my bar a little low.” Roger gave her a sly look and she seemed unfazed.

“I've heard the stories. This still seems like too much though.” She pumped a small amount of whatever was in the bottle onto the back of her hand. “Taking bar bets and acting as courier is one things but this, this is a whole different beast. Are you into cross-dressing?”

“To some extent, I guess.” He sat back down in the chair and Diva pulled up a seat next to him.

“I think it's a little more than “to some extent,” buddy.” She took a brush and ran it over his face in sweeping motions, balancing the rest of the makeup on her lap.

“Okay, so I've always wanted to try it and the idea makes me feel... powerful, y'know.” He relaxed and leaned towards her. “Everyday, I get to be Roger Wilco, goof and dimwit who's only ever saved by pure, blind luck. That character is nice to be and it's certainly who I am-” he paused so she could get the skin around his lips, “-but there's something appealing about a female persona. To be someone completely different, a pretty girl who's got all the boys' attention and is seen as graceful and dangerous. It's something that I just can't be outside of playing a part. It's a taste of life I've never had. I've never been wanted like that.”

“So the 50 buckazoids is just a catalyst for something larger.” She took a pot of something shimmery and blue and covered his eyelids in it.

“I guess.” He flinched when her hand came close to his eye.

“I'm going to apply a little bit of the eyeshadow under you eye just look up and hold still.” The brush she used was small but fluffy and left glitter residue everywhere it so much as came near. “So what's your game plan for playing this femme fatale character you've dreamed up.”

“I could walk down the bar, that'd be kind of intimidating.” Roger hadn't exactly thought this through, but that wasn't exactly something he was known for.

“If you avoided knocking over any glasses or bottles, that would be bad ass as hell.” Diva dusted pink glitter on his cheeks and collar bone. “Close your eyes so I can do your eyeliner.”

Her hands were incredibly steady and she worked quickly creating eyeliner that winged out just a little at the ends.

“I look pretty cute, don't I?” He caught a glimpse of himself in the mirror.

“We're not done yet. Look up-” she gingerly worked mascara into his bottom lashes, “-look straight at me.” She gave his upper lashes a few brush strokes. “Lip stick next...” She snatched a tube from her pile of products on her lap.

“Can I do that on my own, I think I know how.” She placed the tube in his hands and he headed over to the mirror. It was harder than he thought it would be, but he got a decently symmetrical shape from the glossy rose color.

“Just one or two extra touches...” Diva worked lightning fast on highlighting his brows and brushing the lightest amount of contour just below his cheeks. When he looked in the mirror, finally giving himself a full overview, things changed. He didn't feel like Roger anymore. He knew that he was the same person and his hair was still the same loose and curly blonde mop as before but it felt longer and looked less messy. He knew he was still the same Roger as before but he didn't feel like it.

“Hey, you still with me, space cadet!” Diva waved a hand in his face.

“I feel different... Like a real girl.” His body was still masculine, flat and top heavy, but everything about him radiated an aura of femininity regardless of it's actual appearance.

“Let's call you Regina. Your neck looks a little bare, how about a choker. Then we'll head right down to the party.” Diva was short. 5'6” compared to now Regina's staggering 6'4” with heels so naturally it was a little difficult for Diva to help with the necklace.

“Perfect. Everything matches. Black velvet choker and black velvet platforms. Are you ready?” Her hand hovered over the ComPost controls.

“I'm ready.”

“Keep on your feet, you look like a fawn trying to walk for the first time.” That nagging voice came back again.

“QUIET!” Diva shouted and the roar of the party softened at least a little. “Miss Regina Wilco has arrived!”

And that's how they got here, the slow yet somehow graceful walk down the plexiglass bar, platformed heels weaving in between martini glasses, cans, and bottles.

“Well you look better than I thought you would...” The engineer, the one who'd started this whole ordeal, chuckles.

“Did you doubt me?” She picked up one foot and placed the closed toe of velvet against his chin, guiding him to look her in the eyes. “I hope, for your sake, I don't hear another word of that sort from you! Do you understand?”

The joking melts from his face. This is not the same Roger that he's used to making fun of during lunch break. Regina, unlike her counterpart, will take no shit.

“Yes, miss.” She moves on, walking down the line and appraising each face she sees, male or female, like she trying to decide which one to buy.

The cute girl from botany seems absolutely entranced.

“Hey, princess!” Regina winks at her.

“You look very nice, ma'am.” She bows her head. It's a sign of deep respect where she's from.

“You're adorable.” The walk continues. There's someone in particular that she's hoping to surprise. She keeps going, around a bend in the path until she sees a section of bar free from any glasses.

“So...” She halts, facing towards the man in front of her but still much higher than him. “Lieutenant Commander,” she lets one leg start to slide off the bar, getting herself into a seated position on the front edge. Most of the surrounding crew have gone quiet. “Care to buy me a drink?”

Sydney looks like his circuits are absolutely fried. His programming, though very complex and allowing for a wide range of synthetic emotions, is having a little trouble processing what's in front of him.

“You still with us, sailor?” She boops his nose and like an on/off button he shakes back to life.

“My apologies Roger, my syntax is just having a little trouble sorting all of this information.” Whatever designer built him obviously wanted his emotions to be realistic, because his cheeks are actually getting florid.

“You're fully functional, right Sydney?” She puts a hand on his shoulder, tracing circles with her thumb.

“Roger, you know that I do my job-” He starts to prattle of his speech about an androids place on a space ship.

“I know very well that you're a wonderful engineer, but the extra bits... The little treats your model comes with. StarCon didn't deactivate those, did they?” At this point quite a large number of people are listening in and at least one person is filming.

“Not like it's a big deal if someone takes a video. There's plenty of graphic evidence to embarrass you already. Just one more thing on the pile.” The voice chuckles and Regina ignores it.

“Well... If I am to assume we're both speaking of the same thing, then no, StarCon made no such alterations. It's actually among my duties to do such... favors for crew members when it's requested and convenient. You are speaking of sex, am I correct?” He is flustered but collected.

“You are correct.” She shimmies down into her friend's lap. “Thank you for your honest answer Lieutenant Commander Sydney, would you care to join me for a drink?”

“Well I have to need for molecular sustenance...” Sydney scans her eyes for some clue to grab onto as to what the hell is happening. Seduction, even the blatant kind, is not something they accounted for in his programming.

“So we'll chat then. I'd like a drink though, if that doesn't bother you.” She shifts a little on his lap, trying to get comfortable. The friction and weight makes his computers whirr, but only slightly, the sensory input leading that part of his system to think that maybe, he'll be needed for something soon.

“Well I didn't know it could do that!” Her voice rumbles slightly as she whispers in his ear, the synthetic flesh under her awakening ever so slightly.

“It's not exactly an on off switch. Meant to mimic the standard humanoid arousal cycle so as to not seem as robotic. I'm sorry if this has caused you any discomfort.” Sydney places a hand on the outside of her leg to keep her from sliding off.

“Oh no, it's no problem at all!” She giggles and tries to wave down the bartender.

The robot is a simple only slightly humanoid machine that runs on a track up and down the bar and spits drinks out of tubing jutting out of it's stomach.

“I'll take a bee's kiss, please.” The machine fills it's request, spitting the milky cocktail into a martini glass.

“That's an odd choice of drink. Last time I discussed alcohol with you, you stated that you had a distinct preference for beer.” Sydney pulls her in tighter as she leans over to grab the drink.

“Beer is good but sometimes it's nice to indulge in something sweeter. I've always liked them but y'know, gotta order a manly drink. I guess now that I'm wearing high heels and a dress I'm not as worried about that.” She is only a little buzzed at this point, having had drank only half of a PBR tallboy before leaving to start this escapade.

“Imposed ideas of masculinity can be oppressive and harmful. I'm rather proud of you for defying them, Roger.” Sydney pats Regina on the back with his free hand.

She's smiling and getting towards the end of her drink and this whole flirty conversation gig apparently isn't working.

“Maybe you need to get a little more physical?” That voice hints at her. I guess sometimes he's helpful.

She wriggles a little bit, intentionally placing most of the weight and friction at the apex of Sydney's legs. He jolts a little, surprised at the sudden change of sensation.

“You alright?” she croons, jokingly.

“Now Roger, forgive me if I'm misreading the situation but I have to ask, do you want me to... oh what's the Terran term... how you say fuck you?” He's completely serious, looking up at her as if this is all business.

“I was hoping you'd ask. Yes, Sydney, I would very much like if you fucked me.” She put down her not quite empty glass.

“There's your money shot! Have fun kid.” The voice fades away. Maybe she'll be alone for this.

“My quarters are quite close to here. If you're ready to leave, we can go there.” He let one hand trace up the small of her back, eliciting a shiver.

“Sounds like a perfect way to top of the night, Sydney.”

**Author's Note:**

> I am literally the only person writing for this since the 90s... Why do I do this to myself?


End file.
